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Open enrollment is coming: a checklist for 1099 workers

Open enrollment is the one time each year you can pick any Marketplace plan. Here's what independent workers should do before it starts, especially with this year's rule changes.

Couple planning together at a laptop in their kitchen

If you drive, deliver, freelance or run your own business, open enrollment is your version of the benefits meeting nobody invites you to. It’s the one stretch each year when anyone can sign up for a Marketplace health plan or switch to a different one, no special reason needed. Miss it, and you usually have to wait a full year unless something big changes in your life.

Open enrollment begins in the fall, and the exact dates depend on whether your state uses HealthCare.gov or runs its own marketplace. Here’s how to get ready so you’re not scrambling at the deadline.

1. Mark the deadlines for your state

Most states use HealthCare.gov, but some run their own marketplace with their own dates, and a few give you extra weeks. The date that matters most is the deadline to have coverage start on January 1, which comes earlier than the final day of open enrollment. Look up your state’s dates now and put both on your calendar.

2. Don’t just let last year’s plan renew

If you already have a Marketplace plan, you may be renewed automatically. That’s convenient, but it can be expensive this year. The extra premium help that many people received through 2025 expired and has not been extended, so what you pay, and what plans are available, may look different. Plans also change their doctor networks and drug lists from year to year. Log in and compare before you let anything renew.

3. Build a realistic income estimate

Marketplace savings are based on the household income you expect for the coming year. For self-employed people, that generally means your earnings after business expenses, not the total you bill.

This matters more than ever. Starting with 2026 coverage, there’s no longer a cap on how much of your advance premium help you may have to pay back if your income ends up higher than you estimated. If your income swings, make a careful estimate, and update it with the Marketplace during the year if things change.

4. Gather what you’ll need

Having this ready makes the call or the application go quickly:

  • Your best estimate of next year’s income, plus last year’s tax return if you have it
  • The ages and ZIP code of everyone who needs coverage
  • The names of doctors you want to keep
  • Any prescriptions you take regularly
  • Your current plan information, if you have one

5. Think about how you actually use care

Marketplace plans come in Bronze, Silver, Gold and Platinum. Bronze usually has the lowest monthly premium but the highest costs when you use care, and Platinum is the reverse. If you see a doctor often or take regular medications, the cheapest premium isn’t always the cheapest plan once the year is over. If your income is on the lower side, a Silver plan may come with extra savings on deductibles and copays.

One newer option worth knowing about: Bronze and catastrophic Marketplace plans now count as HSA-eligible, so you may be able to pair one with a health savings account and set money aside for medical costs tax-free.

6. Get help if it feels like a lot

You can enroll on your own, or work with a licensed agent who can enroll you in the same Marketplace plans and check whether you qualify for savings. Agents are typically paid by the insurance company, not by you.

The bottom line

Open enrollment is short, and this year comes with real changes. Check your state’s deadlines, compare plans instead of auto-renewing, and build a careful income estimate. A little prep now can save you money and stress all year.

Rules current as of September 2026 and may change. Your advisor can confirm what applies in your state.